


Perks of Being Dean of Winchester, Knight of Hell

by ehre_wahrheit



Series: Adriar's Fic Challenge [3]
Category: Supernatural
Genre: Abaddon as a big sister, Angel! Castiel, Angel! Michael, Arranged Marriage, Cas has wings, Dean is the Knight of Hell, Dean was raised as Luci and Cain’s little baby, Demon! Dean - Freeform, Everyone in Hell at least, F/M, Historical AU where nothing is real or accurate, Human! Adam Milligan, Human! Sam, I haven’t tagged it, I’m drunk off of caffeine, I’m so sorry, Jealousy, John is actually cool, M/M, Michael dirty talks, Mike and Dean are bruhs, Mike has wings, Mojo - Freeform, Oh My God, Other, Plotting, Possessive Behavior, Smut, Somehow Adam is Mary’s kid too, Time Difference, Wtf am I doing, a tad bit of angst, because Dean & Mike being bros are cool, break-ups, but - Freeform, dean has wings, everyone loves Dean, except the demons he likes bullying, hahahahaha, he's a cool dad, i guess, idek, mojo abuse, oh god make this madness stop, oh yeah, relationships, wingkink, yeah - Freeform
Language: English
Status: Completed
Published: 2014-07-17
Updated: 2014-07-17
Packaged: 2018-02-09 06:50:59
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 6,036
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1973034
Author URL: https://archiveofourown.org/users/ehre_wahrheit/pseuds/ehre_wahrheit
Summary: <blockquote class="userstuff">
              <p>Dean's family dies, and he is taken to be cared for by Lucifer and Cain of Hell. When he was old enough, he goes to Heaven to live with his betrothed. Eight hundred years later he goes to Earth and meets the Winchesters of present time: and everything he's ever known is shaken to its core.<br/>-<br/>(It doesn't help that he's in love with his betrothed's youngest brother)<br/>(Or that his betrothed is in love with <em>his</em> youngest brother)<br/>-</p>
            </blockquote>





	Perks of Being Dean of Winchester, Knight of Hell

**Author's Note:**

> Michael and Dean are together at the beginning of this whole thing—as I’ve mentioned in the tags, I was drunk off my ass in caffeine and lack of sleep while I wrote this, and so I’ve had to add the whole first half of it for anything to make any sense. You’ll actually see the exact points where I wrote shit as I was high, and the exact points when I edited it while I am sober. Just fair warning though: this is the first part, so mostly it's major point is on Michael and Dean's relationship, minor on Sam and Gabe's, and only gives us a snippet on the Destiel and Midam. :3
> 
> I can’t do porn properly, sorry. Warning, though: Michael and Dean have sex (once graphically, probs several more times though only implied) before Dean and Cas, Michael and Adam do. Um. I told you, total madness. 
> 
> I honestly don't even know what I'm doing anymore. HAHAHAHAHAHAHA. I enjoyed this though. Madness.  
> \--  
>  **Title:** Perks of Being Dean of Winchester, Knight of Hell  
>  **Word count:** 6,050 (This part only)  
>  **Pairing:** Michael/Dean Winchester, Castiel/Dean Winchester, Michael (Supernatural)  & Dean Winchester, Gabriel/Sam Winchester, Lucifer/Cain, John Winchester/Mary Winchester, Abaddon & Dean Winchester,  
>  **Tags/Warnings:** Arranged marriage, Relationships, Break-ups, Plotting, A tad bit of angst, Historical AU where nothing is real or accurate, Mike and Dean are bruhs, because Dean  & Mike being bros are cool, Demon! Dean, I guess, Angel! Michael, Angel! Castiel, Human! Sam, Human! Adam Milligan, hahahahaha, I’m so sorry, I’m drunk off of caffeine, Dean was raised as Luci and Cain’s little baby, idek, Dean is the Knight of Hell, Oh my god, Abaddon as a big sister, everyone loves Dean, Everyone in Hell at least, except the demons he likes bullying, oh god make this madness stop, oh yeah, I haven’t tagged it, but, wingkink, Dean has wings, Cas has wings, Mike has wings, Somehow Adam is Mary’s kid too, time difference, mojo, mojo abuse, Michael dirty talks, WTF am I doing, jealousy, possessive behavior, smut,   
> **Collections:** Adriar’s ‘Write This Stuff’ Challenge 2014  
>  **Challenge:** No. 5: Something modern + something historical (Exes being the best bros evah + arranged marriage)

Dean of Winchester, Knight of Hell first met his betrothed when he was a mere boy of nine years. He had been the orphan of the late Lord John of Winchester, Legend of the Men of Letters, and Mary of Campbell, Heiress to the land of the Hunters for five years. He had lost his mother and his younger brother, one Sam of Winchester, to a house fire that had been set by no other than the man who had brought Dean to the men who raised him.

It has been of no wonder why it was Dean who survived: his soul had been one of brightness and righteousness that, when Lucifer, Ruler of Hell, and his Chosen, Cain, who had been Dean’s predecessor as Knight of Hell, first laid eyes on him they had hissed and looked away. Dean’s bringer, a Prince of Hell, Azazel, had burnt to the ground when Dean’s soul reached out and began searching for nurturance. Lucifer had sneered, then, thinking human souls to be so _needy_ as to require to be nurtured by another in order to develop and survive—but Cain had no qualms. With his eyes shut and squeezed tight, he had reached for the crying boy and allowed his own tainted, darkened soul to be used for the brightness of Dean’s.

Hell had a war with Heaven at that time, and with Dean’s soul reacting not by _darkening_ but by _growing_ , they allowed themselves to think they have found a way to end the war. Lucifer, dark as he is, was still a creature of love and adoration: he had wanted the war over as much as anyone in their right minds as well. His older brother, Michael, Prince of Heaven and the strongest archangel in existence, had mourned the loss of such bright soul as Dean: and so, as a way to end the war, Cain agreed on turning Dean under his tutelage into the sole Knight of Hell in promise of marriage to Michael of Heaven.

When Dean was nine years old, he didn’t even _understand_ why everyone seemed to busy themselves for a visit that no one actually seemed happy about. He had just continued on with his life: meaning, bullying the lower class demons and the businessmen and pointing out to souls damned to Hell why they actually _deserved to be in Hell_.

He was surprised when Abaddon, another Prince—Princess? It wore the body of a beautiful woman—of Hell picked him up from Alistair’s lair and all but dragged him to his rooms. He pouted, as he was wont to do as a child, and sulked even more when Abaddon cackled and chucked his chin.

“Now, now, my Knight,” she chided, running sharp, blood-red nails down his scalp and across his hair almost affectionately, if Demons could express affection, “you would not disappoint Father, would you?”

Dean perked up. _No_ , he did not want to disappoint Father: he was beautiful and bright and patient, but he was also scary when he was angry. He had seen how the King of Hell’s wrath can destroy a whole league of lower demons—he’d destroyed one, _all because they had hurt Dean._ It was Father’s way of showing love, and concern, but Dean could not understand why or how it could mean to be those two beautiful emotions when it caused so much grief. It was Dad who had had to clean up the mess afterwards, giving Dean a tight smile before beginning his work.

“But why would this be so important?” He was frowning. He was still confused— _why_ was this so important? Who was visiting?

But his demon version of an older sister simply smiled—a grin, really—and ran her hand through his hair again, cooing when he pushed back to her ministrations. “Oh, you will see soon, my Knight.”

“Dean,” he whined. It was a hopeless argument, and they both know it. Father did not want anyone calling Dean ‘Dean’—he had wanted to be the only one, until Dad pushed and pushed until Father agreed, and so there were only two beings in all of Hell allowed to call Dean his given name. Everyone else must address him as ‘my Knight’.

“Your dressers will be here soon, my Knight,” Abaddon finishes, pulling her hand back and cackling again at Dean’s pouted lips. “You must be prepared _impeccably_ for this meeting. _Oh_ , how I wish to be the one to prepare you myself—you would be so _beautiful_.”

Her voice had taken a wistful tone—and Dean shook his head because he _didn’t_ want Abaddon—or any of his siblings, for that matter—to be dressing him. They did, once—and they called him the _Princess of Hell_ as they dressed him in female clothing and fixed him up in such a way that made him cringe today.

Abaddon sighed before he retreated permanently, and Dean was allowed a two second reprieve before his dressers came.

They were silent and efficient as they worked—no one wanted to touch Dean for _any_ length of time longer than necessary. Father was _very_ , very possessive—even of his Son, who wasn’t _even_ his son. Thinking was giving Dean a headache, and so he allowed himself to drift and be lulled into a light doze by the ministration and pampering of six demons.

“My Knight,” one of them said softly, shaking his shoulder. “You are ready—you must now proceed to the Main Halls, my Knight.”

Dean groaned bet got up—surprised to see himself garbed in the formal clothes of Hell, and he gulped in trepidation. He shook himself one last time before moving out of his rooms, down the hall, up the staircase and down another corridor to the large wooden doors that led to the Main Halls.

It was filled with… something beautiful—something he has never felt before, and before he lost his nerve, he opened the door and allowed himself in.

He froze right at the threshold.

“Ah, my Knight, my Son—my Dean of Winchester, Knight of Hell, welcome.” It was Father speaking—Father, who was not on his usual place at the head of the long table, but instead on the seat of the right hand man—with Dad beside him and giving him a look that told him to move.

He bowed first, not letting his eyes stray to the man who _was_ sitting at the head of the table. “My liege,” he muttered, before straightening up. He made his way to the right side of the table, where he usually sat—but no, he was directed to the _left_ —why was he being directed to the left, he wasn’t a left hand, _his place was on the right_ —and then he was sitting, and Father was smiling at him proudly.

“You look wonderful, Dean,” Father complimented, and he bowed his head because _no_ , Father will always be more beautiful than Dean, and it’s impossible for him to be worth such praise. “I would like you to meet my older brother, Dean. This is Michael, and he is your betrothed.”

Dean’s head snapped up because— _what_? He looked at his Father in confusion and then dawning horror, watching as his Father’s eyes twinkled in amusement. He felt his face turn into a scowl before he moved it towards Michael—and—

He swallowed.

_I mustn’t think this way_ , he thought fervently, trying to dissuade his thoughts from forming into coherency, because _it is wrong._ This man—he cannot be seen as more beautiful than Father. Father is the most beautiful Angel there is—was—ever will be—but Michael was… Michael was _bright_ , a burning beacon of light and love and righteousness and Dean could feel the light of his own soul drawn towards him.

He shot a look of panic to his fathers, who were both smiling secret smiles, and then to Michael—

Michael must have been a beautiful human, too. He had a sharp jaw, a high nose, beautiful steel-grey eyes, and full lips. He was smiling at Dean. He swallowed again. He blinked, and when he looked to his fathers, his face was blank, completely empty of emotions.

“I’m going to marry him,” he said, because even as a nine year old child he was old enough to understand _some_ of these things.

Father rolled his eyes in fond exasperation. “Yes, Dean, you will.”

Dean swallowed for the third time, quite audibly now, before looking down at the wood of the table.

_He was going to get married._

 

**..--..**

 

That had been _centuries ago_ —he and Michael were probably engaged for a good six hundred ninety seven years! They had watched as the world rose and fell, as societies built themselves up and ultimately destroyed themselves as well—watched as people climbed and rolled, and it was beautiful, it really was.

They were living in the modern world now—all because Dean could _not_ live in Heaven any longer than he has to.

“I _swear_ , Mike,” he mutters, watching as his fiancé flew around Heaven leading his army. When Dean arrived in Heaven at the ripe age of eighteen—after he’d been killed and brought back as a demon, of course—it did not repel him as he’d thought it would. It _welcomed_ him—warmed that spark of humanity left in his soul that Michael claimed to be the only part of him that he loved.

_Liar,_ he thinks smugly.

“I am feeling _so_ ignored right now!” he whines—because really? They’re home. They don’t have to do anything. _And his fiancé is ignoring him_.

Michael appears before him and Dean gives him a salacious smile, resting his hands against Michael’s hip and pulling him close. “All you’re after is the satisfaction of your libido,” Michael mutters, but he’s smiling, and that’s what matters. “Which,” he adds, pulling back to avoid Dean’s lips, “I must say is _never_ actually satisfied.”

“Mike,” Dean whines again, pouting this time, and Michael chuckles before giving him the kiss—long and deep and dirty—he’d been craving for since he woke up this morning. “Let’s move to Earth,” he asked softly, watching the play of light across Michael’s face. “Please?”

Michael raised an eyebrow. “You’re _asking_?” he says, as if Dean _doesn’t_ —actually, Dean asks for a lot of things. He asks for _so many things_ he is afraid Michael is abusing his powers just to get them.

Dean huffs, drops his hands from Michael’s hips and groans. “ _Why_ do you keep on avoiding the question when I ask it?” he asks, sending Michael a baleful glare. “I mean, I ask. I do it properly, and then _you’re_ the one evading everything. _What is wrong with wanting to move to Earth?_ ”

Michael sighs, his own hands working themselves towards Dean’s waist—his thumbs rubbing gentle circles into Dean’s skin. “We’ll move _soon_ , Dean, I’ve promised you—but I cannot leave my siblings squabbling on their own here, can I?”

Dean sighs as Michael presses a chaste kiss against his lips. “Alright,” he concedes, but he wraps his arms around Michael’s shoulders, pulling him closer and deepening the kiss and growling when Michael makes a move to get away.

“Dean,” he groans, trying to push away, but—

“ _No_ ,” Dean growls back, grinding his hips against Michael’s and relishing in the shudder than runs through the archangel’s body. “You owe me. I woke up without you in bed.”

Michael sighs. “Can we at least move this where my younger siblings _don’t_ get traumatized by watching me?”

Dean grins, but Michael sees it and, with a flap of his wings, they’re back in their rooms. Dean lets out a huff of breath as he falls on his back against the soft bed, feeling the warm, reassuring weight of Michael on top of him as they slowly strip each other of their clothes. Not that they had much in the first place—all Michael had on were his day clothes, and with one flick at the belt around his waist and a pull of the thread behind his neck, it billows down to the floor. Dean is wearing nothing but his drawstring pants—and that is divested quickly as well.

Michael pushes Dean down on the bed forcefully, watching with intent as Dean unfurls his wings. Dean’s wings are, unlike those of his lower class species, aren’t membranous or leathery—they’re made of _feathers_ , only sharper around the edges as if each single one had been scorched. They coloration was the same: it was dirty blond in the undersides, just like Dean’s hair; and it turned darker and deeper in color until it bleeds into the blood red feather of the tips.

Michael watches, awed, as he himself lets out his own wings—all six of them, and Dean grins as he grabs onto the lowest, smallest ones—the most sensitive wings in Michael’s set. Michael hisses out a breath, but he, too, grabs onto the feathers on the underside of Dean’s wings, before leaning down and crashing their lips together.

Michael tastes like ozone and lightning and something tangy that Dean had come to associate to Michael in the past several hundred years—and he moans as he feels his future mate’s (no, they _haven’t_ mated yet, thank you very much) hands press against the flesh of his wings and waves of pleasure zing through his body.

His cock is now steadily leaking precome, and he’s moaning as Michael retaliates on his earlier advances by grinding their hard cocks together harshly.

He gasps and—well, the thing everyone should know about Michael is that is cock is _huge_. No, that wasn’t just Dean’s bottom tendencies—that was him being _honest_ , because Michael _was_ huge. If anyone should know, seriously, Michael, Archangel, Sword of Heaven and most powerful angel in existence, was the very embodiment of ‘ _huge, fat cock_ ’.

Dean had had the honor of being split open on that cock before, and the image of it now—

He moans when he feels two fingers breach him with no warning. He starts rutting up against Michael’s thigh, still smoothing his hands against Michael’s wings, and he moans again when Michael hits his prostate, because _wow._ God (HAHAHAHAHA) he could do this forever. They probably would. He grins at the thought—

“Mike, I’m gonna come,” Dean moans, arching his back when Michael uses four fingers instantly without even patiently stretching with a third—thank fuck for Demon and Angel mojo because _fuck_ , he’d be crying his eyes out had he been human. “Mike, I’m gon’ come if you keep—” his back arcs and his mouth falls open in a silent scream as Michael mercilessly prods against his prostate, his hips still grinding up against Michael’s thigh.

Michael leans down to breath against his ear, and he’s breathing deep and harsh as he fucks Dean open with his fingers. “You can come, Dean,” he says, his voice low and filled with promise, “but here’s the thing. I’m not stopping. You can come, but I’m still going to fuck you. I’m going to pound into you while you’re oversensitive until you’re sobbing and begging me to stop—”

“ _Mike!”_

“—but I’m not gonna stop. I won’t stop until I come, fill you up and plug that hole so my come doesn’t come out until I let it out. Do you understand, Dean?”

Dean nods frantically and tries to stave off his orgasm—because really, demon or not? Oversensitivity is not something he wants to play around with. He sighs in relief when Michael withdraws his fingers—still doesn’t mean that he’s happy about it tho—and then Michael is thrusting in hard and fast and brutal and _right on Dean’s prostate_ and he’s so big—Dean fills so full, so good—

He comes, his back arching off the bed and his chest pressing against Michael—and the archangel starts moving.

He starts moving and he _really means what he said_ —because Dean is beginning to feel oversensitive and the fucker is cheating because he’s using his wings to tickle Dean’s nipples and— _god_ , he can’t take any more, Mike has to stop, _please_ , it’s too much—

It feels good, but it’s too good, it’s painful, it hurts—and Michael is still pounding into him, hard and fast and brutal, and Dean doesn’t really want him to stop, oh god, no—

“—just _take_ it, don’t you? Even when _you’re_ inside me—” he jabs at Dean’s oversensitive prostate three times in a row and makes Dean scream “—you still let _me_ set the pace. You’re such a little _slut_ —but that’s who you are, aren’t you? I’ve watched you, you know, while you were human. Luring pretty little things into your bed but you remember Lady Rhonda? How you just felt _delicious_ in those lacy silk things that even while you’re coming inside her all you can think was that you wanted those panties to yourself? Hmm?”

Michael was dirty talking. It was so rare—and only when Dean had been particularly naughty—but it was gratifying, and Dean’s cock is twitching but—

Dean wails, Michael hitting his prostate again and again and again while his wings move over his skin and make him even more hyperaware that he’s now sobbing, begging Michael to _please come, please, please, please_ —

And Michael stills, groaning into Dean’s neck as Dean sighs in contentment when he feels warmth spreading inside of him. He sobs one last time when Michael pulls out—sobs even harder when Michael pushes back in a plug, _of course he wasn’t kidding about the plug_ , and then they’re kissing and Michael is taking care of him and it’s perfect.

 

**..--..**

 

Dean, as it usually happens anyway, takes out his frustration the following week on demons wrecking havoc. What peace Father and Dad had managed to reign was heightened by Dean’s consent to live with Michael in Heaven—but sometimes, like now, some demons think the Knight of Hell is nothing but a myth and begin trying to dispel the balance that has the world in its usual order.

He starts with the lowest demons—the demons that run around and do the dirty work of scoping out places for hunters and traps. And then he goes for the businessmen—the crossroads demons—who are cheating their contracts in order to take more souls in faster than the allotted time. That is unfair, and really. This is _Hell_ , they have fucking dignity!

Last but not the least, he takes out the Rack: or the members of the Rack who torture souls who aren’t supposed to be tortured. And then he goes to see his Father and Dad because he _misses them, god dammit_ before leaving for Heaven again.

Michael had been evading the question of living on Earth. Again. And Dean is beginning to question his decision to make decisions with Michael by his side because— _come on_. He’s been asking for _one hundred twenty three years_ , couldn’t he be humored? He hasn’t even asked for anything more that whole time!

He doesn’t go straight back to Heaven once leaving Hell, though. Instead, he goes to what is now Lawrence, Kansas, his birthplace and also where his human parents had died. He goes there because of John and Mary Winchester, who shouldn’t be existing but they somehow do, and he watches them as they move around their home. They’ve just gotten married—but he can see that Mary is heavy with child, and he smiles wistfully. Had he not been the beacon that he was when he was younger, would he have grown up human? Would he never have known how it feels to be a demon, to be an angel’s lover?

He sighs and spreads his wings.

Better not dwell on what could—should—have been.

He flew up to heaven.

 

**..--..**

 

Twenty years.

Twenty years is what it finally took Michael to agree to living on Earth—and, well, a whole decade of not seeing Dean because the Knight of Hell insisted that he stayed in Hell. In truth Dean just wanted to get away—because, _really_? _This_ was the definition of soon? They may be immortals—oh, uh, yeah they are—but the thing is, Dean is a very impatient _demon_. What he wants to happen, he wants to happen _immediately_.

But they’re together now.

Well, they’re together _again,_ which is quite weird, but they’re both okay with that—except. Except there’s one thing—Michael brought with him one of his younger brothers. Dean hadn’t—couldn’t have—listened properly to the explanation as to _why_ he was there, just that he _had to be there_ , and all Dean could think was, ‘ _that’s one angel’._

And so the dilemma of the Knight of Hell’s life began. One would think that his dilemma would be Hell but no—no, ruling Hell was _easy_ , it was uncomplicated and simple and mindless. What was _hard_ though was the utter impossible threat of attraction to Michael’s younger brother.

Castiel had been born around the same time Michael was, really, but he was younger by a few thousand years—a few moments in their measurement of time—but he looked so _young_ and vulnerable and like a stupid puppy sometimes that it was all Dean could do to reach out and touch him.

But Michael was keeping a keen eye on the both of them, and hey. He had a fiancé. He was supposed to be angel married. Why they weren’t already, he could only guess—but he wasn’t going to mess this up.

And so life when on for them for the next couple of years: Michael and his penchant for possessiveness; Dean’s trips to Hell for a little bit of R & R; and the sexual tension that is almost always in the air when Cas was in the same room as Dean of Winchester, Knight of Hell.

And it was slowly becoming more and more difficult to stop himself from _taking_.

 

**..--..**

 

What messed everything up, really, was Gabriel.

He’d been missing for millennia—even longer than Dean was alive, actually—but he suddenly appears, but not only that: he brings Sam Winchester, eldest son of the modern world’s reincarnation of Dean’s parents, and he almost falls over when Sam introduces himself.

“God fucking dammit,” he hisses, glaring daggers at Gabriel because, _really_? Everything was good—everything was fine and good and here comes this asshole who tries to ruin it all. Shit!

“Gabriel,” Michael glowers, and then Sam is taking defense and he’s trying to fucking _defend_ Gabriel and Dean almost snaps.

“Sammy,” he says, as calmly as he can, “step away from that angel and _please_ close your eyes.”

“Did you just call me… Sammy?”

That dispels the unfriendly tension because… because _yeah_ , he just called this stranger the name he and his dad—he was human, and only four years old, but he could remember—used to call his baby brother when he was in the crib, and all three angels look at Dean with wide eyes and Dean looks at Sam and he’s pained because, as much as he wants to, _this_ is not his brother—his brother died in the house fire.

“I’m… sorry,” he finally tries, licking his lips as he hides the First Blade back into the plane of reality where he keeps it. “I—” he clears his throat. “That’s what my dad and I used to…” he swallows, catches the look Castiel sends him, and smiles wryly up at Sam. “Tell you what—it’s story time.”

“Oooh, me likey,” Gabriel says immediately and everyone rolls their eyes, but then there are pastries and warm chocolate and _no one cares._

Dean sits between Michael and Castiel—making sure he’s touching both angels—and Sam sits in front of them while Gabriel sits on the floor munching on candies and Dean takes a deep breath and begins.

He begins to tell Sam about Lord John of Winchester, Legend of the Men of Letters; about Mary of Campbell, Heiress of the Hunters; about the house fire that killed them and their younger son, Samuel of Winchester, but allowed their eldest to live, who was now the Knight of Hell.

He tells Sam about how childhood was for him: consisting of mainly playing with Sam, really, and talking to his dad, and when Dean looked at Sam he always used to call him Sammy because that’s what Dad used to call him, and the soft smile that always passed Mary’s face when he saw his kids playing and the way her eyes grew wide the one time Dean was bitten by a snake.

(He survived, obviously, because he won’t be the Knight of Hell if he died.)

He begins to tell Sam about what happened in Hell: how he was raised, _who_ raised him, and how every single day for those eighteen years he missed the baby brother he never got to really enjoy and the parents he lost too early and left too suddenly to even mourn properly. He tells about the wonders of Earth he was able to see and explore himself in those eighteen years before Lucifer killed him and Cain brought him back to life; how he had taken to calling them Father and Dad respectively after they slaughtered a whole league of demons for trying to take him apart because of _jealousy_.

He tells—this time not just Sam, but—all of them about his time in Heaven, discovering the different Heavens of people and just learning how everything works; how everything awed him and made him want to learn even more even though he’d always, always claim he hates reading; how he still wants to go back but he decided to stay on Earth because it was the life he hasn’t experienced properly yet, and would like to; and he tells them about the family in Lawrence, Kansas who looks just like the family he lost almost eight hundred years ago that he would give _anything_ to get back to, but probably will never get the chance.

And then Sam, out of nowhere, begins to talk about his life.

He tells them about growing up as the big brother, knowing about his younger brother, Adam, and falling in love with him quickly simply after seeing him once; he tells them about growing up playing ball with his father and learning how to cook with his mother and how they’ve always had this haunted look about them whenever they talk about wanting a third child; he tells them about how he met Gabriel and really, they’re together—that’s all Dean needs to know.

“Do you…” Sam begins, and then he hesitates, sending a look to Gabriel, before he plunders on. “Would you like to meet them? Mom—Mary and John, that is. And Adam, too—he’s all grown up now, on his way to graduating college.”

Dean smiles. “I don’t know, Sam,” he says, flicking his eyes into the swirls of black and red and white that is his demon’s form that he can show before going back to green, “do you think they’d want to see their child of another lifetime turned out to be like this?”

“You never know,” Sam says softly, and that look he sends Dean is what does him in.

He takes a deep breath. “Yeah, okay, I’ll meet them.”

 

**..--..**

 

No, that’s not where the chaos starts; but meeting Sam is the catalyst for all the shit that’s going to happen next.

The first time, he goes alone. It won’t do well to be meeting your own parents—or, versions of them anyway—for the first time and stringing along your fiancé and the love of your life right?

… _wait._

_Dean. Winchester. What. The. Fuck._

He’s still at the house—more importantly, _still making out with Michael_ because neither of them has gotten laid for the better part of one whole year—that’s a long time, considering they used to fuck on a near daily basis, sometimes even _more times than one_ a day. But now he’s here—just two hours away from the time he’s supposedly about to go visit his parents, on his fiancé’s lap, thinking, _this isn’t the love of my life._

“Dean?”

He is snapped back to reality by Michael’s voice—and oh _god_ , that voice, that’s the voice he’s been getting off to for _eight hundred years,_ why is one measly little angel changing _every fucking thing_?

“Dean, are you alright?” Michael asks, a wisp of concern actually winding into his voice, and Dean shakes his head. He shoves his face into Michael’s neck and presses a kiss there.

“Shit,” he says. “I’m sorry.”

Michael sighs—a long, world weary sigh like he has been expecting something like this—but when Dean pulls away he’s smiling. “Go on and prepare for your visit, Dean.”

“Mike—”

“Dean.”

Dean glares at him for a good second because, _Jesus fucking Christ, I’m literally the son of Hell and I’m acting this way,_ but he shakes his head and gets up anyway. He goes upstairs, and prepares for the visit he has been trying to _not_ think about this whole time.

When he walks out of the bathroom—still damp and warm, covered only by a towel from the waist down—he walks right into no one else but Castiel, who immediately brings this tingly weird sensation in his belly that makes him feel warm all over.

“Dean,” Castiel says, and _oh god,_ _that_ was the voice he’s wishing he could have gotten off to all this time. He swallows, quite audibly, and then remembers _he’s supposed to be getting married to this guy’s older brother,_ so he just gives Castiel a tight smile and moves away, back towards the bedroom he and Michael share.

He sighs against the door once he has it closed behind him, before shaking his head and dressing in the smartest things he can think about: which are a pair of Michael’s trousers and, also, one of Michael’s button up shirts.

_Angels are such presumptuous dicks,_ he thinks, but he thinks so fondly—remembering the kind of look he’d probably given Cas when he arrived, Holy Tax Accountant garb and all. He buttons up his—Michael’s—shirt and straightens out the front before thinking better of it and grabbing his leather jacket, too.

And then he takes his phone, his wallet, his keys; and then he’s giving Cas a hug—if it was longer than usual, _and_ out of Michael’s sight, then that’s for him to know and no one else—and pressing a chaste kiss against Michael’s mouth before he’s out.

The drive to the Winchester home—it’s actually weird thinking of it like that, like they’re different units when, technically, they’re the same—takes the better part of a whole hour, and he’s thankful he cancelled what should—could—have been a hot session with Michael earlier. He would’ve been late, and that would’ve been _so_ embarrassing.

 But he still gets there in time, thankfully (ignoring the little joke Dad—Cain—sent him telepathically five minutes away from the front door). He is a Knight of Hell, he reminds himself—and maybe the world at large, too. He _doesn’t_ get nervous.

He knocks, twice, and the person who greets him is the most beautiful woman he has ever seen. He forces a smile onto his face, because he doesn’t want to cry—and really, how fucking melodramatic. A demon, crying over seeing the version of his mom he never got to see.

“Mary,” he whispers, but then her welcome smile turns into a squint of suspicion before she swats him on the arm with her towel.

“That’s Mom for you, boy,” she answers, voice just as soft—and wow. He grabs her up in a big bear hug, which has her giggling and him straining not to cry—and then there’s a man behind him smiling formally and introducing himself as ‘John’ and Dean has to grin because _oh no,_ _you won’t be John for much longer_.

The third person he sees is Sam, who—of course—is cuddling on the couch with Gabriel, but he greets them anyway and then he’s meeting Adam, who he likes because he’s a sarcastic little piece of shit and _that’s the humor that will get you to hell,_ he doesn’t say. Ahem, offence much?

He spends one whole day with the Winchester family—them relearning about who he is, and he relearning to be part of their family. When he tells them about his childhood, Mary cries and tells him about the first child they never had—and he comforts them by saying, ‘I’m here now,’ which he thought would never work but actually would.

 

**..--..**

 

He goes to visit Hell after the Winchester home. Father and Dad tease him relentlessly about his crush on Castiel—and they both approve, they say, because the war is over and the wedding is all but void anyway. Hell is scared of Dean, Heaven is ruled by Michael—really, they don’t even have to be together anymore.

If Dean grins happily at that, well…

…don’t tell Michael.

 

**..--..**

 

The next time Dean visits the Winchester family, he _does_ bring his fiancé and the love of his life. They’ve been awkward around one another, but Michael seemed unfazed whenever Dean stares too long at Cas or whenever Dean _almost_ says Castiel’s name instead of Michael’s during the heat of the moment.

Dean of Winchester, Knight of Hell, doesn’t miss the look Michael passes with his youngest brother the day they are introduced. He exchanges a grin with Gabriel, and then with Castiel, and somehow he’s grinning at Michael, too—and that’s how they know they’re all okay.

 

**..--..**

 

Michael and Dean break up that evening, but they still live together—and they begin to devise a plan they call, ‘Seduce my ex’s youngest brother’, which was fun and all until they both get hot and bothered by the plans they lay out for their respective targets and end up fucking it out before they fall asleep.

The morning after _isn’t_ as awkward as Dean expected—it was actually fun. The whole plan began and centered around Castiel, of course, because _everyone loves Castiel_. Dean’s plan? Lewd jokes. He has educated the little angel in pop culture and therefore he knows when he and his older brother are making lewd jokes, and so that is what Dean and Michael do the whole day: send each other jokes and innuendo whenever they can with Castiel in the room.

It usually gets the poor little thing hot and bothered, which is actually the point—and Dean smiles gleefully whenever he catches Cas’s eye and gets to stick a spoon in his mouth because _he’s a fucking demon,_ he’s a master at seduction.

 

**..--..**

 

Two days later, Castiel snaps.

He grabs Dean by the scruff of his collar, pushes him up against the wall—and all Dean has time for is a quick smirk before his mouth is being _ravaged_.

 

**..--..**

 

Michael plans a more _subtle_ attack on Adam: body language. Dean is as blatant a predator as humans portray demons, but Michael chooses to _engage_ his angelic prowess to drive Adam up the wall. After Michael moans around a piece of pie—courtesy of Mary Winchester—and blushes as if he were bashful, Dean begins to see _just how much more effective_ subtlety really is.

As a demon he’s never really thought about it: demons were monsters, no questions asked; they need not hide behind façades and carefully drawn masks. But the way Adam stares at Michael, hungry and desperate _even_ with John in the room looking nonplussed—it makes Dean itch to try.

 

**..--..**

 

Adam, also, snaps two days later. But, seeing as he is not as strong as the archangel, all he does is flop himself right onto the angel’s lap to proceed to _devour_ the man’s mouth.

Needless to say, John rolls his eyes and mutters something along the lines of, ‘ _All my sons end up gay for angels. Who would have thought.’_

**Author's Note:**

> There will be three more parts in this: one that is centered on Destiel, another on Sabriel, and the last on Midam.  
> -  
> But, you know. I can live with hate, too. HAHAHAHAHAHA. Hit me up at [ Tumblr ](http://peur-van-dunkelheit.tumblr.com) if you hate me, my fics, or just my existence. Or you can give me prompts.  
> -  
> I swear I'm giving up on my brother's prompts now. THIS IS ACTUALLY FUNNY. I SWEAR, GUYS, I WAS LAUGHING THE WHOLE TIME I WAS REREADING IT AFTER FALLING ASLEEP AND WAKING UP SOBER.  
> -  
> I hope you enjoyed (stay tuned for the other parts!)


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